Substituted 2-(3-aminophenoxymethyl)imidazolines

Abstract

This invention relates to novel substituted 2-(3-aminophenoxymethyl)imidazolines which are useful for the treatment of diarrhea and useful as analgesics.

What is claimed is: 
     
       1. A compound of the formula: ##STR28## wherein R 1  and R 3 , each being the same or different, are: (a) hydrogen; or (b) alkyl or 1 to 6 carbon atoms, inclusive; wherein R 2  and R 4 , each being the same or different, are:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; with the proviso that R 1  and R 2  may not both be hydrogen; wherein R 5  is hydrogen;   wherein R 6  is:     (a) alkanoyl of 2 to 7 carbon atoms, inclusive; or   (b) alkoxycarbonyl of 2 to 7 carbon atoms, inclusive; wherein R 7  is:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; wherein R 8  is alkyl of 1 to 6 carbon atoms, inclusive;   wherein R 9  is:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; or a pharmacologically acceptable salt; the compound being either hydrated or unhydrated.     
     
     
       2. A compound according to claim 1 having the formula: ##STR29## 
     
     
       3. A compound according to claim 2 wherein R 9  is hydrogen. 
     
     
       4. A compound according to claim 3 wherein R 1  is alkyl of 1 to 6 carbon atoms, inclusive. 
     
     
       5. A compound according to claim 4 having the formula: ##STR30## wherein Z is: (a) alkyl of 1 to 6 carbon atoms, inclusive; or (b) alkoxy of 1 to 6 carbon atoms, inclusive;   
     
     
       6. A compound according to claim 5 wherein Z is alkoxy of 1 to 6 carbon atoms, inclusive. 
     
     
       7. ethyl N-[3-[1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy]-2-methylphenyl]carbamate, a compound according to claim 6. 
     
     
       8. ethyl N-[3-[1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy]-2,4-dimethylphenyl]carbamate, a compound according to claim 6. 
     
     
       9. A compound according to claim 5 wherein Z is alkyl of 1 to 6 carbon atoms, inclusive. 
     
     
       10. N-[3-[1-(4,5-dihydro-1H-imidazol-2-yl)ethoxy]-2-methylphenyl]acetamide, a compound according to claim 9. 
     
     
       11. A compound of the formula: ##STR31## wherein R 1  and R 3 , each being the same or different, are: (a) hydrogen; or (b) alkyl of 1 to 6 carbon atoms, inclusive; wherein R 2  and R 4 , each being the same or different, are:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; with the proviso that R 1  and R 2  may not both be hydrogen; wherein R 5  is:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; wherein R 6  is:     (a) hydrogen;   (b) alkyl of 1 to 6 carbon atoms, inclusive,   (c) alkanoyl of 2 to 7 carbon atoms, inclusive; or   (d) alkoxycarbonyl of 2 to 7 carbon atoms, inclusive; wherein R 7  is:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; wherein R 8  is (CH 2 ) n  OR 10  ;   wherein R 9  is:     (a) hydrogen; or   (b) alkyl of 1 to 6 carbon atoms, inclusive; wherein R 10  is:     (a) hydrogen; or   (b) alkanoyl of 2 to 7 carbon atoms, inclusive; wherein n is an integer of 1 to 6, inclusive; or a pharmacologically acceptable salt; the compound being either hydrated or unhydrated.     
     
     
       12. A compound according to claim 11 having the formula: ##STR32## 
     
     
       13. 3-[1-(4,5-dihydro-1H-imidazol-2-yl)-3-hydroxypropoxy]-2-methylbenzenamine, a compound according to claim 12.